Methanesulfonyl chloride → Methyl 3-[2-[(methylsulfonyl)oxy]ethyl]-1-naphthalenecarboxylate

HRID 337603노트

반응식

HRID 337603 반응식
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.CCN(C(C)C)C(C)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:27][S:28]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:30])=[O:29]

참가 물질

5

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66896170Methyl 3-(2-hydroxyethyl)-1-naphthalenecarboxylate

생성물 1

HCID 86651673Methyl 3-[2-[(methylsulfonyl)oxy]ethyl]-1-naphthalenecarboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a dichloromethane (0.03 M) solution of methyl 3-(2-hydroxyethyl)-1-naphthalenecarboxylate (1 eq.) from Step 2, Amine 31 and Hunig's base (1.5 eq.) was added at 0 methanesulfonyl chloride (1.3 eq.). The resulting solution was stirred at 0° C. for 30 min and then at RT for 15 min. The reaction mixture was subsequently quenched with 10% aq. HCl. The aqueous wash was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, and filtered. Concentration of the filtrate in vacuo afforded the crude title compound as a colorless oil.

후처리

  1. waitat RT for 15 min
  2. customThe reaction mixture was subsequently quenched with 10% aq. HCl
  3. washThe aqueous wash
  4. customwas separated
  5. extractionback-extracted with ether
  6. washThe combined organic extracts were washed further with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-000c422fc2324db0bf00c579bcb36652
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889714B2

반응 노트

불러오는 중…